Sodium Hydroxide → HCID 23667709, compound

HRID 1091228Notes

Reaction equation

HRID 1091228 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][SH:10])=[CH:5][CH:4]=1.[OH-].[Na+:12]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][S-:10])=[CH:5][CH:4]=1.[Na+:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 804074-Methoxy-alpha-toluenethiol

Product 1

HCID 23667709HCID 23667709, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(4-methoxyphenyl)methanethiol is stirred in ethanol with sodium hydroxide to form sodium (4-methoxyphenyl)methanethiolate. An equivalent of 1-(chloromethyl)-4-methoxybenzene is added to the mixture, which is stirred overnight. The reaction mixture is then quenched by addition of dilute acid and the product bis(4-methoxybenzyl)sulfide. Subsequently, the bis(4-methoxybenzyl)sulfide is reacted with HBr in acetonitrile to cleave the methoxy protecting groups, followed by neutralization and purification of the bis(4-hydroxybenzyl)sulfide product.

Sources & evidence

ORD record
ord-a7e7e8ad180a446dad57bbe98539aaaa
Source dataset
uspto-grants-2012_03
Patent number
US08129357B2

Reaction notes

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